Category: pyridine-derivatives

Electric Literature of 108-99-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 108-99-6 as follows.

10 g of catalyst B was taken into a cylindrical fixed bed reactor with an inner diameter of 25 mm, and the plunger pump was pumped into a solution of 3-methylpyridine in carbon tetrachloride. The mass ratio of 3- methylpyridine to carbon tetrachloride was 1: The weight hourly space velocity of 10,3-methylpyridine is 6h, the chlorine gas flow rate is 2L/min, and the 3-methylpyridine and chlorine gas are vaporized by the preheating tube and then passed into the fixed bed reactor. The fixed bed reactor is used. The temperature was 400 C, the reaction was carried out for 4 h, the reaction product was passed through a condenser, and 2987 g of the reaction product mixture was obtained in a receiving tank. The ammonia solution was added to adjust to neutrality, and the pear-shaped funnel was separated to obtain an organic phase. 30 g of anhydrous sulfuric acid was added to the organic phase. Magnesium is dehydrated, suction filtered, and then rotary evaporated to remove carbon tetrachloride to give a pale yellow liquid. After analysis and detection, the product is a mixture of 2-chloro-5-trichloromethylpyridine, 2,3-dichloro-5-trichloromethylpyridine and 2,3,6-trichloropyridine, respectively. 77%, 16%, 7%. It is indicated that it is difficult to remove trichloromethyl group under the reaction conditions in the absence of water

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,108-99-6, its application will become more common.

Reference:
Patent; Chongqing Zhong Bang Technology Co., Ltd.; Xue Yi; Li Xueyong; Mu Dengyou; Chen Honglong; Qian Yong; (7 pag.)CN109734657; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 15862-37-0, name is 2,5-Dibromo-3-nitropyridine. A new synthetic method of this compound is introduced below., Formula: C5H2Br2N2O2

tert-Butyl 4-[(5-bromo-3-nitropyridin-2-yl)amino]piperidine-1-carboxylate. 2,5-Dibromo-3-nitropyridine (0.200 g, 0.71 mmol) was dissolved in DMSO (3 mL) and treated with 4-amino-1-boc-piperidine (0.428 g, 2.14 mmol.) The mixture was heated at 80 C. overnight and then diluted with ethyl acetate (30 mL.) The organic solution was washed with water (3*25 mL), saturated sodium bicarbonate (25 mL) and brine (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by automated flash silica gel chromatography (ISCO Redi-Sep column) eluding with 0-100% ethyl acetate/hexane to yield the title compound. 0.229 g (80%). HPLC (method A): Rt=11.2 min. MS: [M+H-t-butyl]+=344.8.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 15862-37-0, 2,5-Dibromo-3-nitropyridine.

Reference:
Patent; Wyeth; US2009/69319; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 147149-98-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows.

4) Methyl 2-methyl-2-[3-(2-trifluoromethylpyridin-4-yl)ureido]propionate 65.6 3.8 ml of a solution of phosgene in toluene (20%) were initially charged under argon. At 75 C., 0.58 g of compound 65.5 dissolved in 20 ml of dry acetonitrile was slowly added dropwise; the mixture was then stirred at 80 C. for 4 h. The mixture was repeatedly concentrated with toluene under reduced pressure. The residue was dissolved in 20 ml of dry tetrahydrofuran and admixed with 0.55 g of methyl amino-isobutyrate hydrochloride. 0.76 ml of triethylamine was slowly added dropwise to this mixture which was then stirred at room temperature for 4 h and then left to stand overnight. The reaction mixture was admixed with water and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 95/5 dichloromethane/methanol. The urea 65.6 was obtained in 59% yield. Molecular weight 305.09 (C12H14F3N3O3); retention time Rt=1.66 min. [B]; MS (ESI): 306.44 (MH+).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine.

Reference:
Patent; SANOFI-AVENTIS; US2009/215728; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 98027-84-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.98027-84-0, name is 2,6-Dichloro-4-iodopyridine, molecular formula is C5H2Cl2IN, molecular weight is 273.8866, as common compound, the synthetic route is as follows.

2,6-Dichloro-4-iodo-pyridine (1 g, 3.65 mmol), N-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-2-pyridyl]acetamide (1 .2 g, 4.58 mmol), PdCI2(PPh3)2 (128 mg, 0.18 mmol) and K2CO3 (1 .51 g, 10.95 mmol) were taken up in 1 ,4- dioxane:H2O:EtOH (6:3:1 , 15 ml) and nitrogen was bubbled through the mixture for 5 min before being heated to 80 C for 2 h. When cooled to rt water (10 ml), brine (10 ml) and EtOAc (25 ml) were added, the mixture stirred vigorously for 5 min and the organic layer was separated. The aqueous layer was extracted with EtOAc (3 x 20 ml) and the combined organics were washed with brine, dried over Na2SO4, filtered andconcentrated. Recrystallization from MeCN gave the product as a solid (760 mg, 74%). MS ES+ m/z 282 [M+H]+.

Statistics shows that 98027-84-0 is playing an increasingly important role. we look forward to future research findings about 2,6-Dichloro-4-iodopyridine.

Reference:
Patent; SPRINT BIOSCIENCE AB; LINDSTROeM, Johan; FORSBLOM, Rickard; GINMAN, Tobias; RAHM, Fredrik; VIKLUND, Jenny; (89 pag.)WO2019/38387; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3978-81-2, 4-(tert-Butyl)pyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, COA of Formula: C9H13N, blongs to pyridine-derivatives compound. COA of Formula: C9H13N

At -20 C, N, N-dimethylethanolamine (8.91 g, 100 mmol, 2.0 eq.) Was added to 150 mL of n-hexane.S-BuLi (80 mL, 200 mmol, 4.0 eq.) Was added dropwise,After the dropwise addition is completed, the reaction is performed at -30 C for 30 minutes.4-tert-butylpyridine (6.76 g, 50 mmol, 1.0 eq) was added dropwise,After the dropwise addition was completed, the reaction was performed at -20 C for 1 hour.Cool to -70 C and add 1,1,2-trifluorotrichloroethane (18.74 g, 100 mmol, 2.0 eq) dropwise.After the dropwise addition was completed, the reaction was carried out at -20 C for 3 hours.The temperature was raised to 10 C and the reaction was allowed to proceed overnight.Pour into 100 L of ice water, extract with EA, wash with water,Column chromatography gave 5.09 g of a yellow solid, yield: 60.0%.

The synthetic route of 3978-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing He Ju Pharmaceutical Co., Ltd.; Pan Guojun; Bai Zhao; (8 pag.)CN110041249; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1101120-05-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 1101120-05-1, name is 3-Formylpyrazolo[1,5-a]pyridine-5-carbonitrile. A new synthetic method of this compound is introduced below.

General procedure: These were made using NaHCO3 or 2,6-lutidine as detailed below, unless otherwise stated. Methylhydrazine sulfate (1.2 equiv) and NaHCO3 (5 equiv) were added to a solution of 3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile (2) (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The solvent was removed in vacuo and the residue taken up in CH2Cl2 and water. The layers were separated and the aqueous phase extracted with CH2Cl2, then the combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. Chromatography or trituration then afforded the hydrazides. Alternatively, methylhydrazine sulfate (1.2 equiv) and 2,6-lutidine (5 equiv) were added to a solution of 2 (1 equiv) in MeOH (5 mL). After all of the aldehyde was consumed, sulfonyl chloride or acyl chloride (1.3 equiv) was added and the reaction mixture stirred for a further 30 min. The hydrazide was then filtered off, washed with MeOH and dried.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1101120-05-1, its application will become more common.

Reference:
Article; Kendall, Jackie D.; Giddens, Anna C.; Tsang, Kit Yee; Frederick, Raphael; Marshall, Elaine S.; Singh, Ripudaman; Lill, Claire L.; Lee, Woo-Jeong; Kolekar, Sharada; Chao, Mindy; Malik, Alisha; Yu, Shuqiao; Chaussade, Claire; Buchanan, Christina; Rewcastle, Gordon W.; Baguley, Bruce C.; Flanagan, Jack U.; Jamieson, Stephen M.F.; Denny, William A.; Shepherd, Peter R.; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 58 – 68;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 19798-80-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 19798-80-2, name is 4-Chloropyridin-2-amine, molecular formula is C5H5ClN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

5.2.2.30 7,8-Dichloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione (30) To a solution of 2-amino-4-chloropyridine (1.28 g, 10.0 mmol) in DMF (40 mL) at -20 C was added NCS (2.67 g, 20.0 mmol). This mixture was allowed to warm to room temperature and stirred for 24 h, and then poured into 300 mL ice-water and extracted with ethyl acetate. The extracts were washed with 1 M NaOH and brine, dried and evaporated. The residue was purified by column chromatography on silica gel to give 4,5-dichloropyridin-2-amine (1.12 g, 69.0%).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 19798-80-2, 4-Chloropyridin-2-amine.

Reference:
Article; Xie, Dongsheng; Lu, Jun; Xie, Jin; Cui, Junjun; Li, Teng-Fei; Wang, Yan-Chao; Chen, Yuan; Gong, Nian; Li, Xin-Yan; Fu, Lei; Wang, Yong-Xiang; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 19 – 32;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 14150-94-8, name is 1-Methyl-3,5-dinitro-1H-pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows. HPLC of Formula: C6H5N3O5

A mixture ofbenzyl (3-oxocyclohexyl)carbamate (247 mg, 0.999 mmol) and 1-methyl- 3,5-dinitropyridin-2(1H)-one (300 mg, 1.507 mmol) in ammonia/MeOH (1M, 6 mL) was microwaved at 90 C for 30 mm to provide a blackish-red solution. Eleven more samples of the same composition were run under the same conditions. The twelve samples were combined and evaporated under reduced pressure. The residue was partitioned between DCM (300 mL) and saturated aqueous NaHCO3 (100 mL). The organic layer was washed with brine (100 mL), dried (MgSO4), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 50% EtOAc in hexanes) provided a mixture of benzyl (3-nitro- 5,6,7, 8-tetrahydroquinolin-7-yl)carbamate and undesired regioi somer benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-5-yl)carbamate as a pale yellow gum. The mixture was used without further purification. MS (ESI, m/z): 213 [M+H]t; j00424J A solution of benzyl (3 -nitro-5 ,6,7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (2.64 g, 8.07 mmol) in ethanol (110 mL) was treated with tin(II) chloride dihydrate (9.10 g, 40.3 mmol) and conc. HC1 (1 mL), then stirred at 80 C for 75 mm. The solution was allowed to cool, then was concentrated under reduced pressure to about 15 mL. The sample was made basic (pH 9) by addition of saturated aqueous NaHCO3; about midway through, the sample was diluted with DCM (100 mL). The mixture was triturated, then filtered, and the filter cake was washed with DCM (50 mL). The filter cake was triturated and sonicated in MeOH (200 mL), then the mixture was filtered. The slightly cloudy filtrate was filtered through Celite 545, then concentrated to provide a yellow solid. Purification by silica gel chromatography (0 to 15% MeOH in DCM) provided a mixture of benzyl (3-amino-5,6,7,8-tetrahydroquinolin-7-yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification. MS (ESI, m/z):298 [M+H]t; 1004251 A sample of benzyl (3-amino-S ,6, 7, 8-tetrahydroquinolin-7-yl)carbamate and regioisomer (1.25 g, 4.22 mmol) was treated with ACN (17 mL). The material was cooled on a dry ice / ethylene glycol bath (approximately -10 to -15 C) and PTSA monohydrate (1.61 g, 8.45 mmol) was added. After stirring 10 mm, a solution of potassium iodide (1.05 g, 6.33 mmol) and sodium nitrite (0.436 g, 6.32 mmol) in water (3.4 mL) was added dropwise over 20 mm. The dry ice bath was replaced with an ice bath, and the reddish-brown mixture was stirred at 0 C for 3 h 40 mm. The solution was diluted with EtOAc (50 mL), cooled on an ice bath and treated with saturated aqueous NaHCO3 until basic (pH 8-9). The organic layer was removed and the aqueous layer was extracted once more with EtOAc (50 mL). The combined organics were washed sequentially with water and brine (50 mL each), dried (Na2504), filtered, treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 23% EtOAc in hexanes) provided a mixture of benzyl (3-iodo-S,6,7,8-tetrahydroquinolin-7- yl)carbamate and regioisomer as a yellow solid. The mixture was used without further purification.MS (ESI, m/z): 409 [M+H]; 1004261 A mixture of t-BuXPhos Pd G4 (76.3 mg, 94.4 tmole), benzyl (3-iodo-5,6,7,8- tetrahydroquinolin-7-yl)carbamate and regioisomer (605.0 mg, 1.482 mmol), tert-butyl piperazine-1-carboxylate (553.5 mg, 2.97 mmol), and sodium tert-butoxide (257.1 mg, 2.68 mmol) was sealed in a 40-mL vial. The atmosphere was evacuated and replaced with nitrogen, three times. Dioxane (15 mL) was added and the solution was stirred at ambient temperature for three days. Material at the same stage from a previous run (from 40.7 mg, 0.100 mmol iodo starting material) was added. The mixture was diluted with EtOAc (100 mL), treated with silica gel, and evaporated under reduced pressure. Purification by silica gel chromatography (0 to 87% EtOAc in hexanes) provided a mixture of tert-butyl 4-(7-(((benzyloxy)carbonyl)amino)-5 ,6,7, 8-tetrahydroquinolin-3 – yl)piperazine-1-carboxylate and regioisomer as a yellow foam. The mixture was used without further purification. MS (ESI, m/z): 467 [M+H]; 1004271 A suspension of Pd/C (10%) (57.1 mg, 0.054 mmol) and the mixture of tert-butyl 4-(7- (((benzyloxy)carbonyl)amino)-5 ,6, 7, 8-tetrahydroquinolin-3 -yl)piperazine- 1 -carboxylate and regioisomer (485 mg, 1.039 mmol) in MeOH (5 mL) was stirred at ambient temperature under an atmosphere of hydrogen overnight. The sample was filtered through Celite 545 under vacuum, and the Celite was rinsed with MeOH. The filtrate was evaporated to provide a mixture of tert-butyl 4- (7-amino-S ,6, 7, 8-tetrahydroquinolin-3 -yl)piperazine- 1 -carboxylate and regioi somer as an orange gum. The mixture was used without further purification. MS (ESI, m/z): 333 [M+H]t; j00428J A solution of tert-butyl 4-(7-amino-S ,6,7, 8-tetrahydroquinolin-3 -yl)piperazine- 1- carboxylate and regioisomer (130 mg, 0.391 mmol) in DCM …

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 14150-94-8, 1-Methyl-3,5-dinitro-1H-pyridin-2-one.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZABLOCKI, Mary-Margaret; GUERIN, David J.; NG, Pui Yee; WANG, Zhongguo; SHELEKHIN, Tatiana; CARAVELLA, Justin; LI, Hongbin; IOANNIDIS, Stephanos; (518 pag.)WO2019/32863; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1129-30-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1129-30-2, name is 2,6-Diacetylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 ml) and 2,6-diacetylpyridine (6g, 36.8 mmol) suspended in diethylene glycol (27 ml_) was cautiously heated to 120 C for 16 hours. The mixture was cooled to room temperature and partitioned between H2O and ether. The ether extracts were washed with 1 N NaOH, dried over MgSO4 and concentrated to a clear oil. Flash column chromatography (0% to 15% EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58%). 1H NMR (400 MHz, CDCI3): 5 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H). 2,6-Diethyl-pyridine has also been prepared as follows:A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 ml_ of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCI2(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether(500 mL).at 0 C unde(r N3 atmosphere. After addition, the resulting mixture was stirred,. , ‘ >.,«?, ‘[‘A V ‘ «’ > ‘ambient temperature oveifngh’tj was then heated to reflux for about 3 hours. The suspensiatonwas poured into cushed ice (200 g) and the mixture was saturated with NH4CI. The organic layer was separated and the aqueous phase was extracted with ether (200 mL x 3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give the product (41 .1 g, 89%).

According to the analysis of related databases, 1129-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2006/18725; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 586-95-8, name is 4-Pyridinemethanol. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H7NO

(i) Reaction of 4-(hydroxymethyl)pyridine with thionyl chloride gives 4-(chloromethyl)pyridine which is reacted with

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 586-95-8, 4-Pyridinemethanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4385058; (1983); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem